Synthesis of Potential Phenolic Metabolites of Benzo[b]fluoranthene

Shantu Amin, Keith Huie, Hussain Nalb, George Balanikas, Stevens G. Carmella, Stephen S. Hecht

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The syntheses of the 12 isomeric hydroxybenzo[b]fluoranthenes (hydroxy-BbF, 1–12) are described. 1-Hydroxy-BbF was prepared by treatment of 1-oxo-1,2,3,3a-tetrahydro-BbF (13) with Pd/C. 2-Hydroxy-BbF was synthesized by reduction of 13 with NaBH4, followed by dehydration, epoxidation, and treatment with Pd/C. 3-Hydroxy-BbF was obtained by reduction of 13 with Zn(Hg) followed by oxidation with Triton-B, dehydration, epoxidation, and aromatization. 4-Hydroxy-BbF and 7-hydroxy-BbF were prepared by reaction of ace-phenanthrylene with 1-acetoxybutadiene, aromatization, hydrolysis, and separation by HPLC. 5-Hydroxy-BbF was synthesized by reaction of o-bromobenzaldehyde with 3-methoxyfluorene, followed by cyclization with KOH and quinoline, hydrolysis, and purification by HPLC. 6-Hydroxy-BbF was obtained by regiospecific cyclization of 3-methoxy-11H-benzo[b]fluorene-11-propionic acid (33), followed by reduction, dehydration, aromatization, and hydrolysis. 8-Hydroxy-BbF was synthesized by dehydration of 7b,8-dihydro-7b,8-dihydroxy-BbF (39). 9-Hydroxy-BbF and 12-hydroxy-BbF were prepared by treatment of the corresponding oxotetrahydro-BbFs with Pd/C. 10-Hydroxy-BbF and 11-hydroxy-BbF were synthesized by reaction of fluorene with the appropriate bromomethoxybenzaldehyde followed by cyclization with hydrolysis.

Original languageEnglish (US)
Pages (from-to)1206-1211
Number of pages6
JournalJournal of Organic Chemistry
Volume51
Issue number8
DOIs
StatePublished - Apr 1 1986

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Metabolites
Dehydration
Aromatization
Hydrolysis
Cyclization
Epoxidation
Purification
Oxidation
benzo(b)fluoranthene

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Amin, S., Huie, K., Nalb, H., Balanikas, G., Carmella, S. G., & Hecht, S. S. (1986). Synthesis of Potential Phenolic Metabolites of Benzo[b]fluoranthene. Journal of Organic Chemistry, 51(8), 1206-1211. https://doi.org/10.1021/jo00358a009
Amin, Shantu ; Huie, Keith ; Nalb, Hussain ; Balanikas, George ; Carmella, Stevens G. ; Hecht, Stephen S. / Synthesis of Potential Phenolic Metabolites of Benzo[b]fluoranthene. In: Journal of Organic Chemistry. 1986 ; Vol. 51, No. 8. pp. 1206-1211.
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abstract = "The syntheses of the 12 isomeric hydroxybenzo[b]fluoranthenes (hydroxy-BbF, 1–12) are described. 1-Hydroxy-BbF was prepared by treatment of 1-oxo-1,2,3,3a-tetrahydro-BbF (13) with Pd/C. 2-Hydroxy-BbF was synthesized by reduction of 13 with NaBH4, followed by dehydration, epoxidation, and treatment with Pd/C. 3-Hydroxy-BbF was obtained by reduction of 13 with Zn(Hg) followed by oxidation with Triton-B, dehydration, epoxidation, and aromatization. 4-Hydroxy-BbF and 7-hydroxy-BbF were prepared by reaction of ace-phenanthrylene with 1-acetoxybutadiene, aromatization, hydrolysis, and separation by HPLC. 5-Hydroxy-BbF was synthesized by reaction of o-bromobenzaldehyde with 3-methoxyfluorene, followed by cyclization with KOH and quinoline, hydrolysis, and purification by HPLC. 6-Hydroxy-BbF was obtained by regiospecific cyclization of 3-methoxy-11H-benzo[b]fluorene-11-propionic acid (33), followed by reduction, dehydration, aromatization, and hydrolysis. 8-Hydroxy-BbF was synthesized by dehydration of 7b,8-dihydro-7b,8-dihydroxy-BbF (39). 9-Hydroxy-BbF and 12-hydroxy-BbF were prepared by treatment of the corresponding oxotetrahydro-BbFs with Pd/C. 10-Hydroxy-BbF and 11-hydroxy-BbF were synthesized by reaction of fluorene with the appropriate bromomethoxybenzaldehyde followed by cyclization with hydrolysis.",
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Amin, S, Huie, K, Nalb, H, Balanikas, G, Carmella, SG & Hecht, SS 1986, 'Synthesis of Potential Phenolic Metabolites of Benzo[b]fluoranthene', Journal of Organic Chemistry, vol. 51, no. 8, pp. 1206-1211. https://doi.org/10.1021/jo00358a009

Synthesis of Potential Phenolic Metabolites of Benzo[b]fluoranthene. / Amin, Shantu; Huie, Keith; Nalb, Hussain; Balanikas, George; Carmella, Stevens G.; Hecht, Stephen S.

In: Journal of Organic Chemistry, Vol. 51, No. 8, 01.04.1986, p. 1206-1211.

Research output: Contribution to journalArticle

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T1 - Synthesis of Potential Phenolic Metabolites of Benzo[b]fluoranthene

AU - Amin, Shantu

AU - Huie, Keith

AU - Nalb, Hussain

AU - Balanikas, George

AU - Carmella, Stevens G.

AU - Hecht, Stephen S.

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N2 - The syntheses of the 12 isomeric hydroxybenzo[b]fluoranthenes (hydroxy-BbF, 1–12) are described. 1-Hydroxy-BbF was prepared by treatment of 1-oxo-1,2,3,3a-tetrahydro-BbF (13) with Pd/C. 2-Hydroxy-BbF was synthesized by reduction of 13 with NaBH4, followed by dehydration, epoxidation, and treatment with Pd/C. 3-Hydroxy-BbF was obtained by reduction of 13 with Zn(Hg) followed by oxidation with Triton-B, dehydration, epoxidation, and aromatization. 4-Hydroxy-BbF and 7-hydroxy-BbF were prepared by reaction of ace-phenanthrylene with 1-acetoxybutadiene, aromatization, hydrolysis, and separation by HPLC. 5-Hydroxy-BbF was synthesized by reaction of o-bromobenzaldehyde with 3-methoxyfluorene, followed by cyclization with KOH and quinoline, hydrolysis, and purification by HPLC. 6-Hydroxy-BbF was obtained by regiospecific cyclization of 3-methoxy-11H-benzo[b]fluorene-11-propionic acid (33), followed by reduction, dehydration, aromatization, and hydrolysis. 8-Hydroxy-BbF was synthesized by dehydration of 7b,8-dihydro-7b,8-dihydroxy-BbF (39). 9-Hydroxy-BbF and 12-hydroxy-BbF were prepared by treatment of the corresponding oxotetrahydro-BbFs with Pd/C. 10-Hydroxy-BbF and 11-hydroxy-BbF were synthesized by reaction of fluorene with the appropriate bromomethoxybenzaldehyde followed by cyclization with hydrolysis.

AB - The syntheses of the 12 isomeric hydroxybenzo[b]fluoranthenes (hydroxy-BbF, 1–12) are described. 1-Hydroxy-BbF was prepared by treatment of 1-oxo-1,2,3,3a-tetrahydro-BbF (13) with Pd/C. 2-Hydroxy-BbF was synthesized by reduction of 13 with NaBH4, followed by dehydration, epoxidation, and treatment with Pd/C. 3-Hydroxy-BbF was obtained by reduction of 13 with Zn(Hg) followed by oxidation with Triton-B, dehydration, epoxidation, and aromatization. 4-Hydroxy-BbF and 7-hydroxy-BbF were prepared by reaction of ace-phenanthrylene with 1-acetoxybutadiene, aromatization, hydrolysis, and separation by HPLC. 5-Hydroxy-BbF was synthesized by reaction of o-bromobenzaldehyde with 3-methoxyfluorene, followed by cyclization with KOH and quinoline, hydrolysis, and purification by HPLC. 6-Hydroxy-BbF was obtained by regiospecific cyclization of 3-methoxy-11H-benzo[b]fluorene-11-propionic acid (33), followed by reduction, dehydration, aromatization, and hydrolysis. 8-Hydroxy-BbF was synthesized by dehydration of 7b,8-dihydro-7b,8-dihydroxy-BbF (39). 9-Hydroxy-BbF and 12-hydroxy-BbF were prepared by treatment of the corresponding oxotetrahydro-BbFs with Pd/C. 10-Hydroxy-BbF and 11-hydroxy-BbF were synthesized by reaction of fluorene with the appropriate bromomethoxybenzaldehyde followed by cyclization with hydrolysis.

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